In this study, the oxidative polycondensation reaction conditions of 4-[(2-hydroxybenzylidene)amino]benzoic acid (4-HBAB) by using oxidants such as air O-2, H2O2 and NaOCl were studied in an aqueous alkaline medium between 40 and 90 degrees C. The structures of the synthesized monomer and oligomer were confirmed by FT-IR, UV-vis, NMR and elemental analysis. The characterization was made by TG-DTA, size exclusion chromatography (SEC) and solubility tests. At the optimum reaction conditions, the yield of oligo-4-[(2-hydroxybenzylidene)amino]benzoic acid (O-4-HBAB) was found to be 68% (for air O-2 oxidant), 70% (for air H2O2 oxidant) 53% (for NaOCl oxidant). According to the SEC analysis, the number-average molecular weight (M-n), weight-average molecular weight (M-w) and polydispersity index (PDI) values of O-4-HBAB were found to be 932, 1469 g mol(-1) and 1.576, using H2O2, and 1895, 2560 g mol(-1) and 1.354, using air O-2 and 2320, 3015 g mol(-1) and 1.300, using NaOCl, respectively. According to TG analysis, the weight losses of 4-HBAB and O-4-HBAB were found to be 96.86% and 73.10% at 1000 degrees C, respectively. O-4-HBAB was shown higher stability against thermal decomposition. Also, electrical conductivity of the O-4-HBAB was measured, showing that the polymer is a typical semiconductor. Electrochemical HOMO, LUMO and energy gaps (E-g) of 4-HBAB and O-4-HBAB were found to be -6.28, -6.36; -2.39, -2.64; 3.89 and 3.72 eV, respectively. According to UV-vis measurements, optical band gap (E-g) of 4-HBAB and O-4-HBAB were found to be 3.23 and 3.09 eV, respectively. (c) 2006 Elsevier B.V. All rights reserved.